This is normal. You are not supposed to stay in Thailand long term on a tourist visa. You have only been able to stay this long because of the Covid extensions. Time to return home and sort out a proper visa for long term stay.
Not good for expats. It says coverage expires upon your return to your country of residence, which is defined as any country you have been 180 days out of 365.
Speaking of pens bring blue ink for Thailand. I have had my signature questioned by government entities because it was in black ink and they asked me to resign in blue ink.
It might be possible but why not get a new passport first. You can enter with the new passport and showing the visa in the old passport. You just travel with both passports.